Process for preparing ceftaroline fosamil

Abstract

The present invention relates to a novel process for preparing ceftaroline fosamil as well as to intermediates of Formulae (1), (3) or (4) of this process.

The invention claimed is: 
     
       1. A compound selected from the group consisting of 
       
         
           
           
               
               
           
         
         wherein 
         R is R 1 —C(O)— with R 1  being C 1-12  alkyl or R 2 —O—C(O)— with R 2  being C 1-4  alkyl, benzyl or phenyl; and 
         Y ⊖  is an anion. 
       
     
     
       2. A compound according to  claim 1 , wherein Y ⊖  is selected from the group consisting of halogenides, trifluoroacetate, methane sulfonate, trifluoromethane sulfonate, toluene-4-sulfonate, tetrafluoroborate, acetate, hexafluorophosphate and hexafluoroantimonate. 
     
     
       3. A process for producing a compound having a formula (4) comprising the steps of:
 (i) reacting [4-(4-pyridyl)-1,3-thiazol-2-yl]thiol with an acylating agent to provide a compound having the formula (ii) 
 
       
         
           
           
               
               
           
         
          wherein R is R 1 —C(O)— with R 1  being C 1-12  alkyl or R 2 —O—C(O)— with R 2  being C 1-4  alkyl, benzyl or phenyl; and 
         (ii) reacting the resultant compound having the formula (ii) with a methylating agent to provide the compound having the formula (4) 
       
       
         
           
           
               
               
           
         
       
     
     
       4. A process of preparing a compound having the formula (3) comprising the steps of:
 (i) reacting 4-acetyl-1-methylpyridinium salt to provide 4-(2-halogenoacetyl)-1-methylpydridinium halogenide; and 
 (ii) reacting the resultant 4-(2-halogenoacetyl)-1-methylpydridinium halogenide with a dithiocarbamate to provide the compound having the formula (3) 
 
       
         
           
           
               
               
           
         
          wherein Y ⊖  is an anion. 
       
     
     
       5. The process according to  claim 4  further comprising the step of:
 (iii) reacting the compound having the formula (3) with an aqueous base to provide a compound having the formula (1) 
 
       
         
           
           
               
               
           
         
       
     
     
       6. A process for producing a compound having the formula (3) comprising the step of:
 (i) reacting [4-(4-(1-methylpyridyl)-1,3-thiazol-2-yl]thiolate with an acid HY to provide a compound having the formula (3) 
 
       
         
           
           
               
               
           
         
          wherein Y ⊖  is an anion. 
       
     
     
       7. The process of  claim 3  further comprising the step of:
 (iii) reacting the compound having the formula (4) by removing the group R— to provide the compound having the formula (1)